Ethanol → HCID 14390560, compound

HRID 2231279Notes

Reaction equation

HRID 2231279 reaction equation
[Br:1][C:2]([Br:19])=[CH:3][C:4]1[S:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15]COC)=[CH:11][CH:10]=2)=[CH:7][CH:8]=1.C(O)C>Cl.O1CCCC1.C(OCC)C>[Br:19][C:2]([Br:1])=[CH:3][C:4]1[S:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 702EthanolHCID 14390570HCID 14390570, compound

Product 1

HCID 14390560HCID 14390560, compoundYield 108.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(2,2-dibromoethenyl)-5-(4-methoxymethoxyphenyl)thiophene (8.8 g, 0.02 mole), prepared by the method of Example 6, ethanol (10 mL), and two drops of concentrated hydrochloric acid in tetrahydrofuran (50 mL) was stirred at room temperature for approximately 18 hours. Gaseous hydrogen chloride was bubbled into the mixture for several seconds, after which 10 mL of methanol was added. The resultant mixture was stirred at room temperature for two hours. This mixture was poured into an aqueous saturated ammonium chloride solution and extracted with diethyl ether. The ether extract was washed with an aqueous saturated ammonium chloride solution. The washed extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure, leaving a solid residue. This residue was dissolved in diethyl ether, and approximately 50 g of silica gel was added to the solution. The mixture was stirred briefly and filtered. The filtrate was evaporated under reduced pressure, yielding 7.8 g of 2-(2,2-dibromoethenyl)-5-(4-hydroxyphenyl)thiophene as a solid (mp 99°-101° C.).

Workup

  1. customGaseous hydrogen chloride was bubbled into the mixture for several seconds
  2. additionafter which 10 mL of methanol was added
  3. stirringThe resultant mixture was stirred at room temperature for two hours
  4. additionThis mixture was poured into an aqueous saturated ammonium chloride solution
  5. extractionextracted with diethyl ether
  6. extractionThe ether extract
  7. washwas washed with an aqueous saturated ammonium chloride solution
  8. extractionThe washed extract
  9. dry with materialwas dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customThe filtrate was evaporated under reduced pressure
  12. customleaving a solid residue
  13. additionapproximately 50 g of silica gel was added to the solution
  14. stirringThe mixture was stirred briefly
  15. filtrationfiltered
  16. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-66bad0e817cb4509a045d0f45ad5629f
Source dataset
uspto-grants-1988_11
Patent number
US04782079

Reaction notes

Loading…